Razor Scooters

Nothing promised more and delivered less than the Razor scooter. Don't let that cool futuristic design fool you. These things were flimsier than skateboards and would send you flying at the smallest crack. That "brake" on the back wheel must have been an inside joke around the factory that somehow made it to production. All that brake did was emit a fluorescent trail of melting-wheel-smoke that would help signal the paramedics at the bottom of the hill.

Sega Dreamcast

The Dreamcast was actually a pretty cool machine. It had good graphics, could connect to the Internet (editor's note: never knew anyone who did this) and had some decent games right at their super cool launch date: 9-9-1999. The only problem was Sony released Final Fantasy VII that same week for Playstation, and it turned out to be pretty sweet. So sweet, in fact, that a lot of people decided they'd rather wait for Playstation 2 instead of buying a Dreamcast. Dreamcast still could have survived, except for the fact that software sales sucked because you could just burn copies of the games with your fancy new CDR drive. Before long, the Dreamcast was dead. Suddenly the $500 bucks you dropped on a system, game, VMU and 4 controllers seemed like kind of a waste.

A Ticket to "Star Wars: Episode 1"

Fuck you, George Lucas. That's pretty much all I have to say about this one. Although the pod racer arcade game is still a good time, so I guess it wasn't a total catastrophe.

Y2K Survival Supplies

When Prince said he was going to "party like it's 1999" he probably wasn't picturing a year's supply of canned tuna and 200 gallons of distilled water. Even more confusing than people's conviction that the end was near was the notion that a trip to Costco would help you live after the apocalypse. And while your stockpiles of canned beans and road flares might come in handy when your drunk and bored one night, the various books/VHS tapes and CD-Roms you bought on survival would almost instantly be useless. The information is still good, it's just that nobody uses VCRs, CD-Roms or books anymore.

Pokemon

Being really into Pokemon wasn't just a waste of money, it was a waste of your future. This show was so stupid, it most likely made you dumber. At the very least, it prevented you from getting any smarter. Then, years later when you casually make a reference to Pokemon at a party you guarantee that nobody within earshot will ever willingly have sex with you. On top of all the real damage Pokemon could do to your mental aptitude and social life, it was a ridiculous waste of money. "Dad, can I have $200 for a card that does nothing?" "No problem, I'm investing in websites that do nothing and it seems to be paying off so far."

Smash Mouth

None of us had to buy Smash Mouth's "Astro Lounge" album in 1999, but a lot of us did anyways. "All Star" seemed like our friend at first. A catchy anthem that would serve as the soundtrack for pool parties and trips to the beach. Then, somewhere around the 500th time you heard it, you were left wondering why you bothered buying the album. There were no other good songs and you were going to hear "All Star" 20 times a day every day whether you purchased it or not. What was once music to our ears became a sad reminder that we helped buy the fat dude who can't sing another cheeseburger and pair of designer sunglasses.

Mars Climate Orbiter

You were probably too busy livin' la vida loca to notice, but in 1999 we invested over 325 million dollars in something called the Mars Climate Orbiter. The point of this mission was to understand more about the climate on Mars, which already seems kind of pointless, but none of that matters because the orbiter exploded before it could come anywhere near Mars. Human error on the programming side confused a unit of measurement, causing the craft to drift off course and get destroyed in the atmosphere. It takes a rocket scientist to make that kind of mistake.

All That Shit You Bought on eBay

Alf keychains. Autographed sports jerseys with no certificate of authenticity. Shoe boxes filled with Pogs. There was no end to the worthless shit you could buy on eBay when it burst on the scene in 1999, and most people were helpless to this new American pastime. The only thing more painful than winning one of these auctions was losing at the last second when someone outbid you by 25 cents. Brave new world, indeed.

A Ticket to Woodstock '99

Woodstock 1999 was everything that the original Woodstock wasn't. It was a corporate sponsored celebration of capitalism that attempted to squeeze some money out of the Woodstock brand. The result is one of the worst music festivals in history. Attendees were subjected to overflowing bathrooms, overpriced food, $4 bottles of water and Limp Bizkit. It's not surprising that they started setting the place on fire, but that's not really in line with whole "peace and love" thing the original concert was all about. Also, people were raped and there was rampant looting and violence. And did we mention Limp Bizkit? All for the low price of $150 +Ticketmaster handling fees! What a bargain!